US4409267A - Method for the finishing treatment of fabric materials - Google Patents

Method for the finishing treatment of fabric materials Download PDF

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Publication number
US4409267A
US4409267A US06/366,761 US36676182A US4409267A US 4409267 A US4409267 A US 4409267A US 36676182 A US36676182 A US 36676182A US 4409267 A US4409267 A US 4409267A
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United States
Prior art keywords
fabric
group
organopolysiloxane
fabric material
silicone
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Expired - Lifetime
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US06/366,761
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English (en)
Inventor
Shoji Ichinohe
Katsusuke Kasahara
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Shin Etsu Chemical Co Ltd
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Shin Etsu Chemical Co Ltd
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Assigned to SHIN-ETSU CHEMICAL CO LTD. reassignment SHIN-ETSU CHEMICAL CO LTD. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ICHINOHE, SHOJI, KASAHARA, KATSUSKE
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the present invention relates to a novel method for the finishing treatment of fabric materials to which pleasant touch of softness and hydrophilicity can be imparted simultaneously.
  • the present invention provides a novel method for the finishing treatment of fabric materials with a fabric-treatment agent containing an organopolysiloxane of a novel type as the effective ingredient thereof.
  • silicones or organopolysiloxane materials are known as a fabric-treatment agent to impart pleasant touch with softness and water-repellency to the fabric material.
  • No silicones are known hitherto, however, which can impart simultaneously pleasant touch with softness and hydrophilicity to the fabric material.
  • silicone-containing fabric finishing agents cannot be used when water repellency of the treated fabric material is undesirable. It is of course possible that an organopolysiloxane is rendered hydrophilic by modifying the molecular structure thereof with introduction of hydrophilic groups. Such a conventional approach of the modification of the molecular structure is not free from the problem that the fabric material treated with such a modified silicone cannot be imparted with desired degree of softness as the other important object of the fabric treatment. Further, on the other hand, the prior art silicone-containing fabric finishing agents with excellent softening effect are not always satisfactory in respect of the adhesion to the surface of the fibers and the hydrophilicity of the fabric materials treated therewith.
  • Another object of the present invention is to impart excellent touch with softness and hydrophilicity simultaneously to a fabric material.
  • Another object of the invention is to provide a novel and improved fabric finishing agent comprising an organopolysiloxane as the effective ingredient thereof, with which fabric materials can be imparted with excellent touch with softness and hydrophilicity simultaneously.
  • the method of the present invention for imparting excellent touch with softness and hydrophilicity simultaneously to a fabric material comprises applying, to the fabric material, a liquid composition comprising, as the effective ingredient thereof, an organopolysiloxane represented by the general formula ##STR1## in which Me is a methyl group; R 1 is a hydrogen atom or a monovalent hydrocarbon group having from 1 to 14 carbon atoms; G is a polyoxyalkylene group represented by the general formula ##STR2## R 2 being a hydrogen atom or a monovalent hydrocarbon group having from 1 to 20 carbon atoms, x being a number of 0, 1, 2 or 3 and y and z each being zero or a positive integer not exceeding 200 with the proviso that y+z cannot be equal to zero; Z is an amino-containing group represented by the general formula ##STR3## a being zero or 3 and R 3 being a substituted or unsubstituted amino group; R is a group selected from R 1 , G and Z; and p,
  • the above described effective ingredient of the slicone-containing fabric finishing agent used in the inventive method is an organopolysiloxane having the polyoxyalkylene groups (II) and the amino-containing organic groups (III) or (IV).
  • This organopolysiloxane represented by the general formula (I) is readily soluble or dispersible in water.
  • the fabric material treated with the fabric finishing agent is imparted with good hydrophilicity and pleasant touch with softness simultaneously.
  • the thus treated fabric material is highly susceptible to the adhesive bonding by use of a hot-melt type adhesive agent contributing to the improvement of the working efficiency.
  • the organopolysiloxane of the general formula (I) has at least one amino-containing organic group Z bonded to the silicon atoms.
  • Such an amino-containing organic group Z can be introduced by the addition reaction of an amine compound of the formula HR 3 with an organopolysiloxane having an epoxy-containing organic group or groups Z' bonded to the silicon atoms, where Z' is an epoxy-containing organic group of the formula ##STR4## R 3 and a being the same as defined above.
  • Such an organopolysiloxane having the polyoxyalkylene groups denoted by G and the epoxy-containing organic groups denoted by Z' may be prepared, for example, by the hydrosilation reaction or dehydrogenation reaction of a corresponding organopolysiloxane represented by the general formula ##STR5## in which R, R 1 , Me, p, q and r each have the same meaning as defined above, with a polyoxyalkylene compound and an epoxy compound having a hydroxy group or an ethylenic unsaturation in the respective molecules in the presence of a platinum catalyst such as chloroplatinic acid.
  • the epoxy compound used in the above mentioned reaction is an expoxy compound having a hydroxy group or an ethylenic unsaturation in the molecule exemplified by allyl glycidyl ether, glycidol, 1,4-cyclohexadiene monoxide and the like.
  • the above mentioned reaction of hydrosilation or dehydrogenation is carried out, preferably, by diluting the organopolysiloxane with an organic solvent which may be an alcoholic solvent, aliphatic hydrocarbon solvent, aromatic hydrocarbon solvent, ester solvent, chlorinated hydrocarbon solvent or the like.
  • an acidity moderator such as potassium acetate may be used in the reaction.
  • the reaction temperature is preferably in the range from -20° C. to 180° C. or, more preferably, from 60° C. to 150° C.
  • the next step is the reaction of an amine compound HR 3 with the thus obtained organopolysiloxane having the polyoxyalkylene groups G and the epoxy groups Z'.
  • This reaction is carried out either by adding the amine compound to the reaction mixture from the hydrosilation or dehydrogenation reaction as such or the organopolysiloxane isolated from the reaction mixture with the organic solvent removed by distillation under reduced pressure.
  • the reaction mixture after the reaction with the amine compound is subjected to a conventional processing procedure such as filtration, stripping of the solvent and the like to give the desired organopolysiloxane of the general formula (I) having the polyoxyalkylene groups G and the amino-containing organic groups Z bonded to the silicon atoms.
  • the amine compound used in the above described reaction is exemplified by ammonia; primary amines such as triethylene tetramine, ethylene diamine, ethylamine, cyclohexylamine, octylamine, allylamine, aniline, benzylamine, phenethylamine, monoethanolamine and the like and secondary amines such as dimethylamine, diethylamine, dibutylamine, N-methylaniline, methyl benzylamine, diphenylamine, morpholine, piperidine, N-methylpiperazine, diethanolamine and the like.
  • primary amines such as triethylene tetramine, ethylene diamine, ethylamine, cyclohexylamine, octylamine, allylamine, aniline, benzylamine, phenethylamine, monoethanolamine and the like
  • secondary amines such as dimethylamine, diethylamine, dibutylamine
  • the amine compound is a silicon-containing amine compound such as 3-triethoxysilylpropyl amine, 3-diethoxymethylsilylpropyl amine, N-(3-trimethylsilylpropyl)ethylenediamine, N-(3-dimethoxymethylsilylpropyl)amine and the like.
  • the reaction of the amine compound with the epoxy-containing organopolysiloxane may be carried out by diluting the reaction mixture with an organic solvent such as an alcoholic solvent, aliphatic hydrocarbon solvent, aromatic hydrocarbon solvent, chlorinated hydrocarbon solvent, ester solvent, ether solvent and others although the reaction may proceed without dilution with an organic solvent.
  • the reaction is usually undertaken under atmospheric pressure but may be carried out under pressurization according to need.
  • the reaction temperature is in the range from -75° C. to 180° C. or, preferably, from 0° C. to 140° C.
  • organopolysiloxane having the polyoxyalkylene groups and the amino-containing organic groups is the effective ingredient in the fabric finishing agent used in the inventive method and the organopolysiloxane is usually used in the form of an aqueous solution or aqueous dispersion which optionally contains various kinds of additives such as emulsifying agents, lubricants, synthetic resins for fabric finishing and the like according to need.
  • the fabric material is soaked with the aqueous solution or aqueous dispersion comprising the organopolysiloxane followed by drying, preferably, with heating.
  • Me and Bu each denote a methyl group and a butyl group, respectively.
  • This organopolysiloxane product had a viscosity of 2,500 centistokes at 25° C., refractive index n D 25 of 1.4450 and amine equivalent of 5,100.
  • a reaction vessel Into a reaction vessel were introduced 350 g (0.8 mole) of a polyoxyalkylene allyl methyl ether expressed by the formula ##STR11## having an average molecular weight of 438, 1,000 g of toluene, 0.1 g of potassium acetate and 0.1 g of a 0.3% solution of chloroplatinic acid in 2-ethylhexyl alcohol to form a reaction mixture and, while the reaction mixture was heated under reflux at a temperature of about 115° C., 735 g (0.067 mole) of a methylhydrogenpolysiloxane expressed by the formula ##STR12## were added thereto dropwise over a period of 1 hour followed by the addition of 23 g (0.2 mole) of allyl glycidyl ether and heating of the reaction mixture under reflux at about 115° C. for additional 8 hours. Thereafter, the reaction mixture was freed of the solvent by distillation under reduced pressure to give a polyoxyalkylene epoxypolysi
  • reaction mixture was freed of the solvent by distillation under reduced pressure followed by filtration to give 950 g of the polyoxyalkylene aminopolysiloxane, referred to as the silicone II hereinafter, expressed by the following formula ##STR13## in which G 2 was a group ##STR14## and Z 2 was a group ##STR15##
  • This organopolysiloxane product had a viscosity of 640 centistokes at 25° C., refractive index n D 25 of 1.4355 and amine equivalent of 2,800.
  • This organopolysiloxane product had a viscosity of 1,700 centistokes at 25° C., refractive index n D 25 of 1.4481 and amine equivalent of 5,300.
  • a reaction vessel Into a reaction vessel were introduced 373 g of a methylhydrogenpolysiloxane expressed by the formula ##STR21## 460 g of the same polyoxyalkylene allyl butyl ether as used in Preparation 1 above, 0.5 g of chloroplatinic acid, 0.1 g of potassium acetate and 600 g of isopropyl alcohol to form a reaction mixture and the reaction was performed by heating the reaction mixture under reflux at a temperature of about 83° C. for 4 hours.
  • a methylhydrogenpolysiloxane expressed by the formula ##STR21## 460 g of the same polyoxyalkylene allyl butyl ether as used in Preparation 1 above, 0.5 g of chloroplatinic acid, 0.1 g of potassium acetate and 600 g of isopropyl alcohol to form a reaction mixture and the reaction was performed by heating the reaction mixture under reflux at a temperature of about 83° C. for 4 hours.
  • This organopolysiloxane product had a viscosity of 665 centistokes at 25° C. and refractive index n D 25 of 1.4435.
  • the silicones I to IV prepared in the above Preparations were used for the finishing treatment of a fabric material to evaluate their effectiveness as a fabric finishing agent in respect of the touch, susceptibility to adhesive bonding and water absorption of the treated fabrics.
  • the silicone V was a polyoxyalkylene-containing diorganopolysiloxane expressed by the formula ##STR23## in which the polyoxyalkylene pendant group denoted by G 5 was a polyoxyethylene group having a molecular weight of about 600.
  • the silicone VI was a dimethylpolysiloxane in the form of an aqueous emulsion containing 30% by weight of the dimethylpolysiloxane.
  • the silicone VII was a polyoxyalkylene-containing diorganopolysiloxane expressed by the formula ##STR24## in which the polyoxyalkylene pendant group denoted by G 7 was a polyoxyethylene-polyoxypropylene copolymeric group having a molecular weight of about 1500.
  • the working solutions for the treatment of the test cloth were prepared each by dissolving 12 parts by weight of a glyoxal resin (NS-18, a product by Sumitomo Chemical Co.), 4 parts by weight of a curing catalyst recommended by the producer of the glyoxal resin (Cat KX, a product by Sumitomo Chemical Co.) and 1 part by weight of either one of the silicones I to VII in 83 parts by weight of water.
  • the amount of the silicone VI in the form of an aqueous emulsion was calculated on the net content of the silicone in the emulsion.
  • test cloth was cut into a test piece of 16 cm ⁇ 16 cm wide and adhesively bonded with a hot melt type adhesive lining cloth of the same size by pressing at 180° C. for 30 seconds under a pressure of 0.5 kg/cm 2 .
  • the thus laminated test cloths were further cut to give 5 pieces of each 12 cm long and 3 cm wide. These test pieces were subjected to the peeling test in an automatic recording tensile tester at an angle of 180° by pulling at a velocity of 30 cm/minute and the values obtained with the 5 test pieces were averaged and recorded as the adhesive bonding strength.
  • each of the silicones I to VII was diluted with water to give an aqueous solution or aqueous dispersion containing 0.5% of the silicone and polyester filaments were treated with this aqueous solution or dispersion in such a manner that the amount of the solution taken up by the filaments was 40 to 50% based on the weight of the dry filaments followed by drying for 24 hours in an air-conditioned room at 25° C. with 60% of relative humidity.
  • the coefficient of static friction of these treated polyester filaments was determined by use of a radar-type instrument for the determination of coefficient of friction.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)
US06/366,761 1981-04-15 1982-04-08 Method for the finishing treatment of fabric materials Expired - Lifetime US4409267A (en)

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JP56056580A JPS57171768A (en) 1981-04-15 1981-04-15 Fiber treating agent
JP56-56580 1981-04-15

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Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4533477A (en) * 1982-12-23 1985-08-06 Wacker-Chemie Gmbh Organopolysiloxanes having SiC-bonded oxyalkylene units and a method for preparing the same
EP0179415A3 (en) * 1984-10-19 1986-07-16 Toho Beslon Co., Ltd. Precursor for production of preoxidized fibers or carbon fibers
US4710405A (en) * 1986-08-25 1987-12-01 Dow Corning Corporation Adhesion of silicone elastomers obtained from aqueous emulsion
US4844888A (en) * 1987-11-13 1989-07-04 The Gillette Company Polysiloxane cosmetic composition
US4915938A (en) * 1987-11-13 1990-04-10 Zawadzki Mary E Hair treating composition
EP0404698A1 (fr) * 1989-06-22 1990-12-27 Rhone-Poulenc Chimie Polydiorganosiloxanes organofonctionnels à fonction amino et polyoxyalkylène
FR2670221A1 (fr) * 1990-12-06 1992-06-12 Rhone Poulenc Chimie Procede pour adoucir et rendre hydrophile une matiere textile dans lequel on utilise une composition comprenant un polyorganosiloxane.
US5158575A (en) * 1990-08-10 1992-10-27 Union Carbide Chemicals & Plastics Technology Corporation Silicone textile finishes
US5252233A (en) * 1990-08-10 1993-10-12 Union Carbide Chemicals & Plastics Technology Corporation Silicone textile finishes
EP0577039A1 (en) * 1992-06-29 1994-01-05 OSi Specialties, Inc. Textile softener having reduced yellowing
DE4222483A1 (de) * 1992-07-09 1994-01-13 Pfersee Chem Fab Organosiloxane mit Stickstoff enthaltenden und mit Äthergruppierungen enthaltenden Resten
EP0804500A4 (en) * 1995-11-15 1998-05-06 Paul E Austin HYDROSILATION OF ESTERS WITHOUT HYDROXYL GROUPS
WO1998049220A1 (fr) * 1997-04-30 1998-11-05 Rhodia Chimie Procede de preparation de polyorganosiloxane fonctionnalise par hydrosilylation et utilisation d'une composition comprenant au moins un polyorganosiloxane pour adoucir et rendre non jaunissante et hydrophile une matiere textile
US6136215A (en) * 1999-09-02 2000-10-24 Dow Corning Corporation Fiber treatment composition containing amine-, polyol-, amide-functional siloxanes
US6153717A (en) * 1997-05-19 2000-11-28 Industrial Technology Research Institute Polysiloxane containing tertiary amine groups and method of preparing the same
US6171515B1 (en) 1999-09-02 2001-01-09 Dow Corning Corporation Fiber treatment composition containing amine-, polyol-, functional siloxanes
US6255429B1 (en) 1999-09-02 2001-07-03 Dow Corning Corporation Amine-, polyol-, amide-functional siloxane copolymers and methods for their preparation
US6307000B1 (en) * 1999-06-18 2001-10-23 Gobal Wealth (Bvi) Ltd Multifunctional nonionic siloxane copolymer for modification of synthetic materials
US6432270B1 (en) 2001-02-20 2002-08-13 Kimberly-Clark Worldwide, Inc. Soft absorbent tissue
US6475568B1 (en) * 2001-05-15 2002-11-05 Crompton Corporation Block, non-(AB)n silicone polyalkyleneoxide copolymers with tertiary amino links
US6511580B1 (en) 2001-11-15 2003-01-28 Kimberly-Clark Worldwide, Inc. Soft absorbent tissue containing derivitized amino-functional polysiloxanes
US6514383B1 (en) 2001-11-15 2003-02-04 Kimberly-Clark Worldwide, Inc. Soft absorbent tissue containing derivitized amino-functional polysiloxanes
US20030035954A1 (en) * 2000-02-29 2003-02-20 Masaaki Miyoshi Synthetic fiber improved in slimness and method for producing the same
US6576606B2 (en) 2001-04-27 2003-06-10 Kelmar Industries, Inc. Hydrophilic non-yellowing organopolysiloxane textile softener compositions
US6576087B1 (en) 2001-11-15 2003-06-10 Kimberly-Clark Worldwide, Inc. Soft absorbent tissue containing polysiloxanes
US6582558B1 (en) 2001-11-15 2003-06-24 Kimberly-Clark Worldwide, Inc. Soft absorbent tissue containing hydrophilic polysiloxanes
US6599393B1 (en) 2001-11-15 2003-07-29 Kimberly-Clark Worldwide, Inc. Soft absorbent tissue containing hydrophilically-modified amino-functional polysiloxanes
US20030211953A1 (en) * 2002-04-25 2003-11-13 The Procter & Gamble Company Durable fiber treatment composition
US20030215411A1 (en) * 2002-04-22 2003-11-20 The Procter & Gamble Company Fiber treatment composition
WO2004014327A1 (en) * 2002-08-09 2004-02-19 Kao Corporation Hair detergent compositions
US20090012257A1 (en) * 2005-02-25 2009-01-08 Dow Corning Corporation Siloxane Copolymers
US20100048795A1 (en) * 2007-04-11 2010-02-25 John Kennan Silicone polyether block copolymers having organofunctional endblocking groups
US8754155B2 (en) * 2005-09-06 2014-06-17 Dow Corning Corporation Delivery system for releasing silicone ingredients
CN104328668A (zh) * 2014-10-16 2015-02-04 河南瑞贝卡发制品股份有限公司 人工合成纤维后整理手感综合助剂及其制备、浸渍方法

Families Citing this family (2)

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JPS59179885A (ja) * 1983-03-31 1984-10-12 松本油脂製薬株式会社 炭素繊維原糸用処理剤
JPS63303184A (ja) * 1987-05-29 1988-12-09 松本油脂製薬株式会社 バインダ−繊維用処理剤

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US3419423A (en) * 1964-10-09 1968-12-31 Dow Corning Adducts of silicon hydride polysiloxanes and hydrolyzable silanes having alkenyl radicals useful for rendering substrates water repellent
US4105567A (en) * 1976-02-12 1978-08-08 Th. Goldschmidt Ag Organosilicon compounds and textile fiber finishes containing them
US4283191A (en) * 1979-03-23 1981-08-11 Th. Goldschmidt Ag Preparation for shrinkproofing wool
US4293611A (en) * 1979-10-22 1981-10-06 Sws Silicones Corporation Silicone polyether copolymers
US4365967A (en) * 1979-12-14 1982-12-28 Ciba-Geigy Corporation Method of treating, especially dyeing, whitening or finishing, textile fabrics
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Cited By (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4533477A (en) * 1982-12-23 1985-08-06 Wacker-Chemie Gmbh Organopolysiloxanes having SiC-bonded oxyalkylene units and a method for preparing the same
EP0179415A3 (en) * 1984-10-19 1986-07-16 Toho Beslon Co., Ltd. Precursor for production of preoxidized fibers or carbon fibers
US4830845A (en) * 1984-10-19 1989-05-16 Toho Belson Co., Ltd. Precursor for production of preoxidized fibers or carbon fibers
US4710405A (en) * 1986-08-25 1987-12-01 Dow Corning Corporation Adhesion of silicone elastomers obtained from aqueous emulsion
US4844888A (en) * 1987-11-13 1989-07-04 The Gillette Company Polysiloxane cosmetic composition
US4915938A (en) * 1987-11-13 1990-04-10 Zawadzki Mary E Hair treating composition
EP0404698A1 (fr) * 1989-06-22 1990-12-27 Rhone-Poulenc Chimie Polydiorganosiloxanes organofonctionnels à fonction amino et polyoxyalkylène
FR2648821A1 (enrdf_load_stackoverflow) * 1989-06-22 1990-12-28 Rhone Poulenc Chimie
US5075403A (en) * 1989-06-22 1991-12-24 Rhone-Poulenc Chimie Amino/polyoxyalkylenated polydioganosiloxanes
US5147578A (en) * 1989-06-22 1992-09-15 Rhone-Poulenc Chimie Amino/polyoxyalkylenated polydiorganosiloxanes
US5252233A (en) * 1990-08-10 1993-10-12 Union Carbide Chemicals & Plastics Technology Corporation Silicone textile finishes
US5158575A (en) * 1990-08-10 1992-10-27 Union Carbide Chemicals & Plastics Technology Corporation Silicone textile finishes
EP0546231A1 (fr) * 1990-12-06 1993-06-16 Rhone-Poulenc Chimie Procédé pour adoucir et rendre hydrophile une matière textile dans lequel on utilise une composition comprenant un polyorganosiloxane
FR2670221A1 (fr) * 1990-12-06 1992-06-12 Rhone Poulenc Chimie Procede pour adoucir et rendre hydrophile une matiere textile dans lequel on utilise une composition comprenant un polyorganosiloxane.
US5277968A (en) * 1990-12-06 1994-01-11 Rhone-Poulenc Chimie Polyorganosiloxane softening/hydrophilizing of textile substrates
EP0577039A1 (en) * 1992-06-29 1994-01-05 OSi Specialties, Inc. Textile softener having reduced yellowing
US5593611A (en) * 1992-06-29 1997-01-14 Osi Specialties, Inc. Method for imparting softness with reduced yellowing to a textile using a low amine content, high molecular weight aminopolysiloxane
DE4222483A1 (de) * 1992-07-09 1994-01-13 Pfersee Chem Fab Organosiloxane mit Stickstoff enthaltenden und mit Äthergruppierungen enthaltenden Resten
US5612409A (en) * 1992-07-09 1997-03-18 Ciba-Geigy Corporation Organosiloxanes having nitrogen-containing and ether group-containing radicals
EP0804500A4 (en) * 1995-11-15 1998-05-06 Paul E Austin HYDROSILATION OF ESTERS WITHOUT HYDROXYL GROUPS
WO1998049220A1 (fr) * 1997-04-30 1998-11-05 Rhodia Chimie Procede de preparation de polyorganosiloxane fonctionnalise par hydrosilylation et utilisation d'une composition comprenant au moins un polyorganosiloxane pour adoucir et rendre non jaunissante et hydrophile une matiere textile
FR2762847A1 (fr) * 1997-04-30 1998-11-06 Rhodia Chimie Sa Procede de preparation de polyorganosiloxane fonctionnalise par hydrosilylation et utilisation d'une composition comprenant au moins un polyorganosiloxane pour adoucir et rendre non jaunissante et hydrophile une matiere textile
US6153717A (en) * 1997-05-19 2000-11-28 Industrial Technology Research Institute Polysiloxane containing tertiary amine groups and method of preparing the same
US6307000B1 (en) * 1999-06-18 2001-10-23 Gobal Wealth (Bvi) Ltd Multifunctional nonionic siloxane copolymer for modification of synthetic materials
US6171515B1 (en) 1999-09-02 2001-01-09 Dow Corning Corporation Fiber treatment composition containing amine-, polyol-, functional siloxanes
US6255429B1 (en) 1999-09-02 2001-07-03 Dow Corning Corporation Amine-, polyol-, amide-functional siloxane copolymers and methods for their preparation
US6136215A (en) * 1999-09-02 2000-10-24 Dow Corning Corporation Fiber treatment composition containing amine-, polyol-, amide-functional siloxanes
US20030035954A1 (en) * 2000-02-29 2003-02-20 Masaaki Miyoshi Synthetic fiber improved in slimness and method for producing the same
US6432270B1 (en) 2001-02-20 2002-08-13 Kimberly-Clark Worldwide, Inc. Soft absorbent tissue
US6576606B2 (en) 2001-04-27 2003-06-10 Kelmar Industries, Inc. Hydrophilic non-yellowing organopolysiloxane textile softener compositions
US6475568B1 (en) * 2001-05-15 2002-11-05 Crompton Corporation Block, non-(AB)n silicone polyalkyleneoxide copolymers with tertiary amino links
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JPS61472B2 (enrdf_load_stackoverflow) 1986-01-08

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